It is a persistent misconception that Cuba's rigid socialist government already provides a solid amount of social aid to its citizens, and travel to the island is challenging for those with U.S. passports. There are ways to travel legally to Cuba as a US citizen, and volunteers from the states can attest that voluntourism to Cuba is increasingly popular.

The premiere episode of the latest season of Anthony Bourdain: No Reservations finds Tony in Cuba, land of cigars, classic cars and Castro, trying to burrow beneath the surface of America's most unknowable neighbor.

Choosing an island getaway shouldn't be dictated by whatever sweet deals the airlines happen to be plugging. There are a whopping 28 island nations and 7,000 individual islands that comprise the Caribbean, and their personalities differ dramatically.